Enter the boat shoe. With the preppy, Ivy style enjoying a wide-reaching resurgence, it was only a matter of time before this polarising piece of footwear was given a stylish reappraisal on dry land. Names such as Sebago have earned a deserved reputation for producing classic nautical-leaning loafers and deck shoes, but now we’re starting to see premium iterations of the style by the likes of Brunello Cucinelli, TOM FORD and Mr P.

“Like red trousers and polo belts, boat shoes have traditionally been a nailed-on indicator of a certain kind of upbringing – and therefore considered to be about as far from the sartorial zeitgeist as something can be,” says the menswear writer and stylist Charlie Teasdale.

“I think the general moccasin shape is great,” he adds. “And though I’m still on the fence about classic, low-slung boat shoes, I’m a staunch advocate for the chunkier, slightly taller variations out there. In truth, I’m coming round to the classic shape, too, as brands begin to demonstrate how they can be worn like a loafer.”

The story goes that the shoe was first designed in Connecticut in the 1930s by Paul A Sperry. Their rubber soles allowing for sure footing on even the slipperiest pontoon or yacht club deck. While the style quickly became an upper-crust East Coast staple, there have been previous examples of the deck shoe being worn in intriguing – and subversive – ways. In 1980s Milan, the paninaro subculture was defined by young men and women embracing and refracting American style: bright puffer jackets, washed-out denim, white socks and classic deck shoes were the de facto uniform, along with a Vespa and a cigarette.

Nostalgia, as ever, has a role to play in the return of the deck shoe. “The Sebago Dockside is the first shoe that I remember wearing to school,” says Drake’s creative director, Michael Hill, who has collaborated with Sebago several times on limited-edition takes on archival deck shoes. “That played a significant role in shaping my view on clothing and style. I’ve always loved the silhouette and what it represents.”

“I wear several different pairs,” says Chris Black, a writer, creative consultant and host of the podcast How Long Gone. “Black leather from The Row, along with other versions in black and brown suede. They are so versatile, working with shorts, jeans, even a casual suit. My mum put me in them when I was kid – everything comes back around.”

Rather than opting for the stiffer, more-traditional approach to preppy style – pastel polo shirts, tight shorts, box-fresh deck shoes and a snooty attitude – stylish guys appear to be creating a more louche approach to incorporating the deck shoe into their summer arsenal. Boxy, oversized shirts, classic crew-neck T-shirts, relaxed linen trousers and tinted sunglasses, giving the whole look a little dash of joie de vivre.

“You want a bit of 1990s-yuppy elegance, rather than the usual, rather staid yacht club style,” Teasdale says. “The kind of thing Paul Newman might have worn on a day off.”